1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 136209283, compound

HRID 876591Notes

Reaction equation

HRID 876591 reaction equation
[C:1]([O:4][C@H:5]([C@H:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH2:20][N:19]([CH3:24])[C:18]3=[O:25])[C:10]1=[O:26])[C:6](O)=[O:7])(=[O:3])[CH3:2].[O:27]=[C:28]1[O:32][N:31]=[C:30]([C:33]2[CH:38]=[CH:37][C:36]([NH-:39])=[CH:35][CH:34]=2)[NH:29]1.CCN=C=NCCCN(C)C>CC#N>[C:1]([O:4][C@H:5]([C@H:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH2:20][N:19]([CH3:24])[C:18]3=[O:25])[C:10]1=[O:26])[C:6](=[O:7])[NH:39][C:36]1[CH:35]=[CH:34][C:33]([C:30]2[NH:29][C:28](=[O:27])[O:32][N:31]=2)=[CH:38][CH:37]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 58181678HCID 58181678, compoundHCID 178514212HCID 178514212, compound

Product 1

HCID 136209283HCID 136209283, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 70-4 (40 mg) in CH3CN (1 mL) at 0° C. was added 4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl amide (21 mg) followed by EDCI (25 mg). The reaction mixture was warmed to rt and stirred for 72 h. The mixture was concentrated under reduced pressure and placed under high vacuum. The crude material was purified by reverse phase HPLC using a C18 column and a gradient of (89.95:9.95:0.1 H2O:MeCN:HCO2H to 9.95:89.95:0.1 H2O:MeCN:HCO2H) to afford compound 70-5 (30 mg) as a white solid. LC-MS: M+H=522.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe crude material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-27daf496f14d40679d140c39c0b58004
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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